Hotels in Chestertown
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Top Rated Chestertown Hotels
Red Roof Inn & Suites Chestertown
160 Scheeler Rd Chestertown MD
Free Cancellation
Reserve now, pay when you stay
0.58 mi from city center
$72 nightly
The price is $80 total per night
$80 total
Sep 23 - Sep 24
Total with taxes and fees
Red Roof Inn & Suites Chestertown features free WiFi in public areas, coffee in a common area, and free newspapers. You can put free parking to good use if you drive. The 24-hour front desk has staff always at the ready. Additional amenities include laundry facilities, a vending machine, and a TV in a common area.
Pet friendly
Parking included
The Lodge at Great Oak Landing
22170 Great Oak Landing Rd Chestertown MD
Free Cancellation
7.76 mi from city center
$124 nightly
The price is $137 total per night
$137 total
Sep 17 - Sep 18
Total with taxes and fees
Guests staying at The Lodge at Great Oak Landing enjoy access to a golf course, a 24-hour gym, and free WiFi in public areas. You can put free parking to good use if you drive. Other amenities at this beach lodge include a seasonal outdoor pool, coffee/tea in a common area, and laundry facilities.
Pool
Parking included
Comfort Inn & Suites Chestertown
150 Scheeler Road Chestertown MD
0.64 mi from city center
$107 nightly
The price is $119 total per night
$119 total
Oct 6 - Oct 7
Total with taxes and fees
Comfort Inn & Suites Chestertown features a gym, free WiFi in public areas, and a business center. If you drive, put free parking to good use. The 24-hour front desk has staff always at the ready. Additional amenities include a seasonal outdoor pool, coffee/tea in a common area, and a meeting room.
Pool
Breakfast included
Historic Inns of Annapolis
58 State Circle Annapolis MD
27.98 mi from city center
$140 nightly
The price is $159 total per night
$159 total
Oct 12 - Oct 13
Total with taxes and fees
At Historic Inns of Annapolis, guests have access to a 24-hour gym, free WiFi in public areas, and meeting rooms. Valet parking is available for USD 50.00 per night, and there's also limo/town car service. The front desk has multilingual staff on hand 24/7 to help with securing valuables, luggage storage, and tours or tickets. Other amenities at this historic hotel include conference space, coffee/tea in a common area, and express check-in.
Pet friendly
Free WiFi
Pendry Baltimore
1715 Thames St. Baltimore MD
28.3 mi from city center
$440 nightly
The price is $517 total per night
$517 total
Oct 11 - Oct 12
Total with taxes and fees
Guests of Pendry Baltimore enjoy a 24-hour gym, free WiFi in public areas, and meeting rooms. Valet parking is USD 65 per night if you plan to drive, or hop aboard the airport shuttle (available 24 hours) for USD 108.39 per vehicle one-way. The 24-hour front desk has staff standing by to help with concierge services, dry cleaning/laundry, and luggage storage. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Other amenities at this luxury hotel include a business center, a seasonal outdoor pool, and a terrace.
Pool
Spa
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
4 Philadelphia Ct Rosedale MD
Free Cancellation
Reserve now, pay when you stay
24.05 mi from city center
$71 nightly
The price is $82 total per night
$82 total
Sep 27 - Sep 28
Total with taxes and fees
Guests of La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh enjoy a gym, free WiFi in public areas, and a business center. Free parking is included with your stay. The 24-hour front desk has multilingual staff ready to assist with concierge services and securing valuables. Additional amenities include coffee/tea in a common area, express check-in, and express check-out.
Breakfast included
Pet friendly
Best Western Plus Hotel & Conference Center
5625 O'Donnell Street Baltimore MD
25.92 mi from city center
$116 nightly
The price is $131 total per night
$131 total
Sep 30 - Oct 1
Total with taxes and fees
Guests of Best Western Plus Hotel & Conference Center have access to an indoor pool, a gym, and free WiFi in public areas. There's free parking and a cruise ship terminal shuttle. The 24-hour front desk has multilingual staff ready to assist with concierge services, luggage storage, and dry cleaning/laundry. Additional amenities include a hot tub, meeting rooms, and a conference center.
Pool
Hot Tub
Hampton Inn Baltimore/White Marsh
8225 Town Center Drive Baltimore MD
Free Cancellation
Reserve now, pay when you stay
23.47 mi from city center
$102 nightly
The price is $117 total per night
$117 total
Sep 22 - Sep 23
Total with taxes and fees
Renovated in 2023, Hampton Inn Baltimore/White Marsh offers a gym, free WiFi in public areas, and a seasonal outdoor pool. Self parking is available for USD 4.10 per day. The 24-hour front desk has staff standing by to help with luggage storage and securing valuables. Additional amenities include coffee/tea in a common area, express check-in, and express check-out.
Pool
Breakfast included
Annapolis Waterfront Hotel, Autograph Collection
80 Compromise St Annapolis MD
Free Cancellation
Reserve now, pay when you stay
27.93 mi from city center
$239 nightly
The price is $273 total per night
$273 total
Sep 30 - Oct 1
Total with taxes and fees
Annapolis Waterfront Hotel, Autograph Collection offers a 24-hour gym, a rooftop terrace, and free WiFi in public areas. Valet parking is available for USD 39 per day. The 24-hour front desk has staff standing by to help with securing valuables, concierge services, and dry cleaning/laundry. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Additional amenities include meeting rooms, conference space, and a 24-hour business center.
Pet friendly
Free WiFi
Hampton Inn & Suites Edgewood/Aberdeen-South
2110 Emmorton Park Rd Edgewood MD
Free Cancellation
Reserve now, pay when you stay
20.73 mi from city center
$84 nightly
The price is $95 total per night
$95 total
Sep 29 - Sep 30
Total with taxes and fees
At Hampton Inn & Suites Edgewood/Aberdeen-South, guests have access to a gym, free WiFi in public areas, and meeting rooms. Free parking is available if you drive. Multilingual staff at the front desk are standing by 24/7 to help with access to locker space, securing valuables, and dry cleaning/laundry. Additional amenities include conference space, a 24-hour business center, and coffee/tea in a common area.
Breakfast included
Pet friendly
Hilton Garden Inn Baltimore/White Marsh
5015 Campbell Boulevard Baltimore MD
Free Cancellation
Reserve now, pay when you stay
23.36 mi from city center
$98 nightly
The price is $113 total per night
$113 total
Sep 27 - Sep 28
Total with taxes and fees
At Hilton Garden Inn Baltimore/White Marsh, guests enjoy features like an indoor pool, a 24-hour gym, and free WiFi in public areas. If you drive, put free parking to good use. The front desk has multilingual staff standing by 24 hours a day to assist with dry cleaning/laundry and securing valuables. Other amenities at this family-friendly hotel include meeting rooms, a conference center, and a 24-hour business center.
Pool
Pet friendly
Quality Inn & Suites Bel Air I-95 Exit 77A
2112a Emmorton Park Road Edgewood MD
Free Cancellation
Reserve now, pay when you stay
20.67 mi from city center
$62 nightly
The price is $70 total per night
$70 total
Sep 27 - Sep 28
Total with taxes and fees
Guests of Quality Inn & Suites Bel Air I-95 Exit 77A have access to free WiFi in public areas. Free parking is included with your stay. Front-desk staff are standing by 24/7 to assist with any requests.
Breakfast included
Parking included
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Stay near popular Chestertown attractions
Cheap Chestertown hotels options
Driftwood Inn
609 Washington Avenue Chestertown MD
$64 nightly
The price is $70 total per night from Sep 17 to Sep 18
$70 total
Sep 17 - Sep 18
Total with taxes and fees
5.4/10 (182 reviews)
Comfort Inn & Suites Chestertown
150 Scheeler Road Chestertown MD
$107 nightly
The price is $119 total per night from Oct 6 to Oct 7
$119 total
Oct 6 - Oct 7
Total with taxes and fees
Where should you stay in Chestertown?
What are some of the best hotels to stay with the kids in Chestertown?
Book one of these hotels for you and the kids in Chestertown. Comfort Inn & Suites Chestertown is a hotel offering free parking, free full breakfast, and laundry facilities. You and your family can also consider Red Roof Inn & Suites Chestertown, a hotel offering free parking, laundry facilities, and free WiFi.
What are the best hotels in central Chestertown?
These are some of the most popular hotels in the center of Chestertown:
- Red Roof Inn & Suites Chestertown is a hotel offering free WiFi, free parking, and flat-screen TVs.
- Comfort Inn & Suites Chestertown is a hotel offering free breakfast, free WiFi, and free parking.
Historical Society of Kent County Maryland and Chestertown Historic District are a couple of sights to visit in the heart of Chestertown.
Chestertown hotels essential information
Accommodation | 1,099 hotels |
|---|---|
Lowest Price | $70 |
Highest Price | $517 |
Popular hotels | Red Roof Inn & Suites Chestertown, The Lodge at Great Oak Landing, Comfort Inn & Suites Chestertown, Historic Inns of Annapolis, Pendry Baltimore, La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh, Best Western Plus Hotel & Conference Center, Hampton Inn Baltimore/White Marsh, Annapolis Waterfront Hotel, Autograph Collection, Hampton Inn & Suites Edgewood/Aberdeen-South, Hilton Garden Inn Baltimore/White Marsh, Quality Inn & Suites Bel Air I-95 Exit 77A |
Recent Reviews
Historic Inns of Annapolis
5/5 Excellent
"Every thing was amazing. The staff was extremely helpful and the parking situation was perfect. Room was top notch."
A verified traveler stayed at Historic Inns of Annapolis
Posted 3 hours ago
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